Pet-friendly holiday rentals in Simpson Bay

4.98 out of 5 average rating, 58 reviews

A white, modern condo complex is set atop a rocky outcrop overlooking a sandy beach. Waves gently lapping at the shore and a clear blue sky serve as a backdrop, creating a serene coastal atmosphere.

Apartment in Simpson Bay

Coral Villa- Steps From BEACH!

Step into our oceanfront paradise on Simpson Bay beach. Just steps away from the sandy coast! Cherish sunrise serenity and late-night tranquility. Relax on the patio, absorb vistas, let waves weave their soothing symphony – a cherished moment! : ) Great location too! Close to Sunset Beach Bar—grab an ice-cold Heineken, watch planes land above. Famous Maho is also a quick stroll (5min from Sunset Bar). food, shops, nightlife, casinos its all there. A perfect location to properly discover SXM!

A bright and modern kitchen area features sleek cabinetry and stainless steel appliances. A dining table with four upholstered chairs is set next to a comfortable sofa, creating an open and inviting living space. Neutral tones enhance the contemporary design.

4.88 out of 5 average rating, 51 reviews

NEW Double S Suite

In the heart of Simpsonbay, close to bars, restaurants, and the beach, you'll find this stylish and newly constructed apartment. Only 4 min from the airport and have double-paned windows to keep out the noise. The apartment has a queen-size bed, free Wi-Fi, and 2 flat-screen TVs; it's also only 2 minutes from Simpson bay beach, known for its clear water. This chic grey and white studio comes with all the amenities necessary for a restful and romantic beach getaway in the middle of St. Maarten.

4.95 out of 5 average rating, 124 reviews

A serene beachfront view is presented through sliding glass doors, showcasing a private terrace with a small round table and two chairs. Palm trees gently sway in the breeze, framing the clear turquoise sea and sandy beach beyond.

Apartment in Marigot

Studio «SeaBird» les pieds dans l’eau sur la plage

Le « studio SeaBird » est idéalement situé avec une vue magnifique sur la mer Caraïbes et une plage idyllique rien que pour vous! Il offre beaucoup de confort et de rangement avec une décoration raffinée et originale. La résidence est parfaitement sécurisée avec une grande piscine et jardin tropical. Tout est accessible à pied: épicerie, marché local, boutiques, restaurants traditionnels ou gastronomiques, gare maritime vers les autres îles, etc... Wifi haut débit et télé Europe et Amérique.

A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.

5 out of 5 average rating, 55 reviews

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at SBYC. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security. Free concierge service included.

4.9 out of 5 average rating, 114 reviews

An infinity pool extends over the edge, offering panoramic views of the lagoon. The tranquil water reflects the blue sky, while steps lead from the pool's edge to the terrace. Lush greenery is visible, enhancing the serene atmosphere of the space.

Guest suite in Cupecoy

Panoramic View Terrace Infinity Pool Top Penthouse

Wake up to the magnificent panoramic view of the lagoon on the top floor, rejuvenate your body with a refreshing dip in the private rooftop infinity pool with a coffee or tropical drink. Take a 10 mins stroll to the famous Mullet bay Beach and grab a few freshly French croissants by the Square. After sunset, enjoy the plentiful neighborhood bars and restaurants or take 5 mins drive to Maho where you will find a vast variety of restaurants, casino and clubs or Porto Cupecoy for romance spot.

5 out of 5 average rating, 103 reviews

A panoramic view of turquoise waters showcases numerous boats anchored in the distance, framed by lush palm trees. A rainbow appears across the sky, adding a colorful touch to the serene coastal landscape.

Townhouse in Cole Bay

Hillside Beach Townhouse Simpson Bay

Dreaming of a gorgeous sunset, turquoise waters and enjoyable nightlife? Welcome to Simpson Bay Beach Front Townhouse where sunny memories are made! Less than 1 minute walking (50meters) from the beach and surrounded by bars and popular restaurants featuring local and international food, spas, shops and casinos! Next to Simpson Bay Beach Resort and Marina where you have departures to different islands with numerous boat charter activities. The location assures that you will have an awesome!

5 out of 5 average rating, 20 reviews

A well-lit bedroom features a spacious bed with crisp white linens and various decorative pillows. Matching bedside tables hold stylish lamps. A wall-mounted television is positioned in front of the bed, while light streaming through partially opened shutters adds a bright touch to the room.

Home in Simpson Bay

The beachcomber

Welcome to your perfect island retreat! Located in the heart of Beacon Hill, this cozy unit offers the ideal home base for exploring all that Sint Maarten has to offer. Just steps away from the island’s top attractions, you'll be within walking distance to: Maho Beach, Casinos,Restaurants & Bars. This unit is perfect for couples or solo travelers. Don’t miss out on the best location on the island – book your stay in Beacon Hill today and live like a local just steps from the action!

4.99 out of 5 average rating, 170 reviews

An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.

Loft

Sea Loft Vue imprenable - piscine privée

* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

4.9 out of 5 average rating, 214 reviews

Apartment in Maho

Maho Love Nest: Unwind by the Rooftop Pool&Hot Tub

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance. If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available for you to indulge.

A bright living area is visible, featuring a comfortable couch and an armchair. The large glass doors showcase stunning ocean views and a spacious balcony, while soft drapes frame the opening, adding to the serene atmosphere.

4.93 out of 5 average rating, 27 reviews

Maho Beach House: Deluxe 1-Bedroom, Oceanview Luxe

Discover our premier corner unit in Maho Beach House, where breathtaking, unobstructed sunset views over iconic Maho Beach await. Step onto the wrap-around balcony for a stunning vantage point over the ocean and watch the planes soar overhead. Inside, you’ll find elegant interiors crafted for relaxation and style. Located in the heart of Maho, everything you need is a short stroll away - Perfect for those seeking a memorable Sint Maarten experience in the heart of the action.

4.96 out of 5 average rating, 75 reviews

Villa in Simpson Bay

Waterfront "Bonjour" Beacon Hill St Maarten

This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator

Home in Upper Prince's Quarter

A modern kitchen and living area are visible, featuring a large island with bar seating, complemented by pendant lighting. Floor-to-ceiling glass doors provide access to an outdoor terrace with ocean views. Natural light fills the space, enhancing the contemporary decor.

5 out of 5 average rating, 20 reviews

Aman Oceanview

The Aman Oceanview is an oasis of calm, luxury and elegance, built into the hillside overlooking the sublime and sparkling Atlantic Ocean and Saint Barth. This a brand new modern property consists of two master bedrooms with two bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. All two bedrooms, the living room have unobstructed views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean, form the focal point of Aman

Popular amenities for Simpson Bay pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.77 out of 5 average rating, 44 reviews

Home in Cole Bay

AnnetsBB, ComfyBed, Gated, Garden, Parking, Washer

5 out of 5 average rating, 19 reviews

Steps leading down to a sandy beach are framed by a white railing. The clear turquoise water laps gently at the shore, revealing a mix of sand and smooth stones. Bright sunlight illuminates the tranquil scene, highlighting the serene coastal atmosphere.

Home

Pelican key - BEACH FRONT Villa

4.94 out of 5 average rating, 31 reviews

A vibrant view of the coastline and distant hills is framed by the greenery of palm leaves and a tall cactus. The blue rooftops of nearby houses contrast with the clear blue water, creating a serene outdoor setting.

Home

NEW House 2 bathrooms, 3 terraces and ocean view

4.93 out of 5 average rating, 15 reviews

A serene coastal view is captured, showcasing the shimmering blue ocean under a clear sky. Lush greenery and well-maintained gardens are visible in the foreground, while white buildings with decorative elements rest subtly along the coastline.

Home in Cole Bay

Blue Palm Estate Townhouse w/ Ocean View

5 out of 5 average rating, 17 reviews

A shaded outdoor seating area features a comfortable sectional sofa and a natural wood coffee table. Tropical palm trees and a view of the pool enhance the space, while loungers are positioned nearby. Soft textiles in muted colors contribute to a laid-back ambiance.

Home

La plus belle vue de l'ile !

5 out of 5 average rating, 17 reviews

A modern living area is showcased, featuring a large white sectional sofa adorned with striped cushions. Colorful abstract paintings are displayed on the walls, enhancing the space. An archway leads to a bright dining area and a glimpse of the kitchen, creating an open and inviting layout.

Home in Lowlands

Villa d’artiste moderne

4.91 out of 5 average rating, 65 reviews

A private pool sits on a spacious wooden deck, surrounded by lush greenery. Lounge chairs are positioned nearby, offering a place to relax. The serene view encompasses a calm body of water and distant islands under a clear blue sky.

Home in Orient Bay

Paradise View, Maison créole avec piscine privée

4.64 out of 5 average rating, 14 reviews

The upper-level house is framed by palm trees and surrounded by a spacious, paved area. A staircase leads to the entrance, while multiple seating arrangements are positioned on the balcony. The blue sky and ample sunlight create a vibrant setting.

Home in Simpson Bay

“Les Medes” 3 bedroom in Beautiful Beacon Hill

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 34 reviews

A dining area features a modern white table set for two, complemented by elegant chairs. Large windows provide a panoramic view of lush green hills and blue skies. A decorative plant adds a touch of nature, enhancing the serene ambiance of the space.

Flat

Magnifique suite S12 à 300m de la mer

5 out of 5 average rating, 18 reviews

A comfortable outdoor seating area is featured, consisting of a white sectional sofa and individual chairs, all accented with red cushions. A small table sits in the center, surrounded by lush greenery and a view of the beach in the background.

Flat in SAINT MARTIN

"Black Pearl"

Villa in Les Terrasses de Cul de Sac

4.96 out of 5 average rating, 28 reviews

Water access, heated pool, kayaks & snorkeling

Apartment in Collectivity of Saint Martin

Two white lounge chairs are positioned on green grass, facing the sandy beachfront. Palm trees sway gently in the breeze, with the clear blue waters of the lagoon visible in the background, framed by a bright, sunny sky.

4.75 out of 5 average rating, 36 reviews

Studio sable et cocotiers

4.74 out of 5 average rating, 123 reviews

Villa in Lowlands

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

4.94 out of 5 average rating, 16 reviews

Flat in Grand Case

Sea View Studio with Infinity Pool – Romantic Stay

Apartment in Sint Maarten

The living area features modern furnishings, including a light sofa, a coffee table, and two armchairs. A dining area with a wooden table is visible, along with large sliding doors that reveal an ocean view and a spacious balcony. Natural light floods the space.

4.96 out of 5 average rating, 28 reviews

Casa Nova, Indigo Bay SXM

Villa in Upper Prince's Quarter

A sunlit outdoor area showcases a serene infinity pool bordered by wooden decking. Lounge chairs are situated under a vibrant red umbrella, offering views of the ocean and lush landscape. Potted plants add a touch of greenery, complementing the peaceful atmosphere.

4.92 out of 5 average rating, 65 reviews

Villa Blue Roc

Private, pet-friendly home rentals

5 out of 5 average rating, 47 reviews

A tranquil view of the Caribbean Sea is captured from a cozy sleeping area, featuring a spacious bed with light-colored linens. The scene is framed by flowing white curtains, leading to a covered terrace adorned with a thatched gazebo and beachside furniture.

Flat

Charming apartment on the beach, 1 or 2 bedrooms

A serene outdoor pool area is surrounded by lush greenery, showcasing multiple lounge chairs and shaded umbrellas. The pool reflects the landscape and is complemented by a backdrop of distant buildings and hills, creating a tranquil setting for relaxation.

Flat in Lowlands

4.85 out of 5 average rating, 26 reviews

Emerald Apt at Maho Beach

4.94 out of 5 average rating, 16 reviews

A light-filled living area features a spacious sofa adorned with neutral-toned pillows, complemented by a small wooden table and a variety of seating. Large windows invite natural light, while a modern kitchen area, equipped with sleek appliances, promotes an open atmosphere with views of palm trees outside.

Apartment

Beautiful Large 2 Bedrooms apartment in Maho

4.88 out of 5 average rating, 24 reviews

A spacious living area features contemporary furnishings, including white sofas and an accent chair, accompanied by a decorative coffee table. A striking mural of a cityscape adds visual interest. Natural light fills the room, enhancing the open layout leading into the dining area.

Flat

Evasion au bord du Lagon

Apartment in Saint-Martin

An aerial view captures a spacious duplex residence with a turquoise pool surrounded by tropical landscaping. The exterior features a light-colored façade and a large terrace adorned with palm trees and sun loungers. Nearby, a shaded area offers additional seating under the greenery.

4.96 out of 5 average rating, 28 reviews

Baie Orientale Cosy Duplex 1

4.89 out of 5 average rating, 28 reviews

A private pool is showcased, surrounded by a sunlit terrace and vibrant palm trees. The turquoise water glistens under the clear sky, with lounge chairs positioned nearby for relaxation. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

Townhouse in Cole Bay

Charming 3BR Villa w Private Pool in Pelican Key

4.91 out of 5 average rating, 58 reviews

A spacious outdoor terrace offers breathtaking sunset views over the ocean. The wooden dining table is surrounded by matching chairs, while potted plants add greenery. A cozy seating area features a large blue chair, enhancing the serene atmosphere of the space.

Apartment in Lowlands

Gorgeous Beachfront PENTHOUSE- Sunset Ocean Views!

Lounge chairs with blue cushions are positioned near the tranquil pool, surrounded by lush greenery. A vibrant umbrella provides shade, while a stone wall enhances the private, serene atmosphere of the outdoor space. Sunlight filters through the leaves, creating a relaxing environment.